The Thieves' Guild (M/F story)

Isabel Blackthorne looked up from her desk as her assistant Samantha knocked on the door. "Michael is here to see you, ma'am. He says that you sent for him?"

Isabel nodded. "I did. Just send him in."

Michael bowed courteously as he entered the room, and she indicated the chair opposite her desk. He was a handsome man with dark hair and green eyes, and was wearing an utterly unremarkable grey tunic. But then again, he never wore anything that was worthy of remark. As leader of the Guild of the Night, Isabel had many competent people at her command, but Michael was special. He could gather information better than anyone, and had a gift for avoiding attention when it was needed – she'd seen him slip past guards more than once by acting like he had every right to be there, without a word ever passing his lips. When she needed a job done quickly, efficiently, and secretly, she knew exactly who to summon.

He sat with a face that looked completely devoid of emotion as he waited for her to tell him why she had summoned him.

"So, how are things working out with your new student?" Isabel asked him.

"Silvia is young, and very inexperienced," he told her. "She makes a lot of mistakes, and often talks before she thinks, but she is eager to learn, and we are making progress. I think she'll be a fine agent one day."

"I've been told that you often have to punish her," Isabel said. "And that you use... old-fashioned methods."

"You mean I spank her," Michael said. "The old ways are sometimes the best, and it has had a wonderful effect on her behaviour. Her promises to do better always sound a bit more sincere while she's nursing a sore bottom."

"You are aware that she's an adult?" Isabel said, raising an eyebrow.

"She's told me that many times – every single time I pull her trousers down and put her across my knee, in fact. But as long as I am her teacher, I will decide how to punish her. Unless, of course, you disapprove?"

She shook her head. "If it works, it works. Anyway, that's not the only reason I wanted to talk to you. Some of our information almost ended up in the wrong hands."

"A spy?" he asked calmly.

"I don't think so. Just a bit of clumsiness, as far as I can tell. I had a meeting with some of the new girls down near the docks recently, and someone left some notes behind when they left. The town guards were in the area afterwards, and they managed to find them – they'd fallen on the floor, I think. I want you to head over to the Watchmen's barracks and pick up the notes. Then, I want you to try to find out who left them behind, and punish her."

"Punish?" Michael said for clarification.

She shrugged. "You seem so fond of your.... old-fashioned methods. You have my permission to employ them on the guilty girl. Give her a good spanking, on the bare bottom. Is that clear enough for you?"

"Crystal."

The next day, Isabel was busy in meetings all day, so it was late afternoon before she could summon Michael again. He entered her office with the papers under his arm, and his usual unreadable expression.

"Did you have any trouble with the guards?" she asked.

"None whatsoever," he replied. "No one looked at me twice."

"So, have you had any luck figuring out who left the notes behind?" she asked.

"The lady in question was kind enough to write her name on them." He placed the paper on her desk, and Isabel turned it over. She blushed as she saw her own name, in her own handwriting, and when she looked at Michael, his normally blank face was displaying a wide grin. "The guild leader herself. Who would have thought?"

"Oh lord," Isabel said as she placed her palm in front of her mouth.

"Now," he said, "I have orders from the guild leader herself to place you across my knee and give you a – what were her exact words?  A good spanking, on the bare bottom? That was it." There was a twinkle in his eye, and it was clear that he found the situation immensely entertaining. "But given the circumstances, I believe I'm going to let you off, just this once."

For a long time, Isabel sat there in silence, until she finally met his gaze. "That's very kind of you, Michael, but no."

"No?" Michael echoed, raising an eyebrow. The grin was replaced with his usual blank slate.

"This oversight, this SLOPPINESS," she said, indicating the papers on the desk, "is a major breach of the rules of the Guild, of the care and attention we pay to every part of our operations. Anyone committing such an infraction deserves to be punished." She sighed. "Anyone. No exceptions."

"And you think a spanking is the best way to punish a forgetful guild leader?" he asked.

She winced. "I'll admit, I'd have probably chosen some other punishment if I'd known my own bottom could be in danger, but I don't see why not. I deserve it." She looked deep into his eyes. "And know this – if I have to be punished, I'm glad you are the one carrying it out."

"I'm flattered."

"So," she said as she rose to her feet, straightening out her black tunic. "How do we proceed?"

"Firstly, unless you want your assistant to hear what's about to happen to your backside, you should probably ask her to go home." Her eyes widened. She'd forgotten about that.

"Samantha?" she said as she opened the door. "Why don't you take the rest of the day off? I'm going to discuss some private matters with Michael." The assistant seemed surprised, but happy at the unexpected end of the workday.

Once she'd made sure that Samantha had left the building, she turned around to see that Michael had sat down on the low bench along the northern wall of the room. "Come here," he said, crooking his finger at her. When she approached him, he regarded her sternly.

"Take your trousers down." With shaking fingers, she lifted her tunic and slowly lowered her trousers to her knees. He reached his hand forward and gently guided her over his lap, and with her face hidden from his view, she could finally show the grin she had been hiding for the past few minutes.

She'd heard the stories about how he'd been treating his new student – how he'd bared her bottom, put her across his lap, and spanked her soundly until she was sore, sobbing, and sorry. How he'd forced her to stand in the corner while he watched her sniffle and think about what she'd done. How he'd taken her out of that corner to finish the job with a brush or a thick strap. And all she had been able to think about was how she had wanted him to do the same to her. But she didn't want to say it out loud – he'd have thought she was mad. So, she'd arranged a small misdeed, 'forgetting' some papers, and asking him to punish the miscreant. And now, she was about to get what she had asked for.

The sting of the first smack caught her by surprise. She'd expected some sort of warm-up, but the smacks that were now impacting her cheeks were anything but gentle.

"Ow!" she said loudly after the first dozen or so smacks. "That stings!"

"That's the idea," he remarked, his hand continuing to pepper her backside. "It's not going to be pleasant, but remember that you asked for it."

"Oh, go ahead," she said, trying to hide how much she was enjoying being over this handsome man's lap, with his hand all over her bottom. "I deserve every smack."

They didn't talk much as he continued to spank her, moving his hand from cheek to cheek, covering her entire bottom in a warm sting. Before long, she was squirming at every smack of his palm.

"I'm very disappointed in you, Isabel." It was the first time he'd used her first name – under the circumstances, it seemed better than 'Miss Blackthorne'. "It's not like you to make such an error. Forgetting papers? Not important ones, I'll grant you, but what kind of example are you setting for the rookies?"

"Ouch!" she yelled as the sting in her bottom grew intolerable. "I'm sorry! It won't happen again, I swear!"

"I'm glad to hear it," he said. Suddenly, his hands moved to her drawers, and he began to take them down. Isabel held her legs together to make sure he didn't see anything she didn't want him to see, but she didn't protest.

As he continued to spank her, Isabel was surprised at how much more his hand stung on her bare bottom. She hadn't thought the thin fabric had provided much protection, but before long, tears were rolling down her face.

She was sobbing loudly and kicking her legs furiously long before he told her to get up. Back on her feet, she tried to rub the sting away, but he slapped her hands away. "Not yet," he told her. He pointed at the nearest corner. "Go stand there with your nose against the wall and your hands on your head."

"F-for how long?" she sobbed as stepped out of the trousers and drawers. They'd already been almost kicked off by her struggling.

"Until I tell you to come out," was the reply.

As Isabel moved into position, any onlooker would have been amazed at the change she had gone through during the afternoon. The proud guild leader with the sharp eyes and the confident smile had been replaced by a sobbing, quivering girl with her bare, red backside on display.

Facing the corner, Isabel could feel her grin returning to her face. Her bottom burned like crazy, but it was somehow an enjoyable burn. And knowing that Michael watched her every move, ready to strike if she reached back to rub her bottom, was a thrilling and erotic. She almost wanted to rub, just so that he could catch her and punish her for it, but she decided against it. If the stories about his treatment of Sylvia had any truth to them, her punishment was far from over.

By the time Michael told her to turn around, Isabel had been so preoccupied that she almost forgot to hide her smile before she turned to face him. As she looked at her punisher, she looked like a very sorry little girl.

"Now, we'll begin the last part of your punishment," he said. In his hand, he was holding a small wooden ruler he'd taken from her desk – the room didn't have many implements, so his choices had been limited.

She whimpered a bit as she looked at the ruler, but didn't complain as he pulled her back over his lap. But as the hard wood struck her bottom, she kicked her legs and squealed as he continued to paint her bottom red. Every stroke of the ruler was followed by a loud wail, and before long, she was sobbing into the bench, unable to summon the strength to beg him to let her up.

Finally, once her entire bottom burned like a campfire, he put the ruler down and helped her up, hugging her close. She cried into his chest as he spoke soothingly to her, his hand running through her hair.

"How are you feeling?" he said after a while.

"Sore," she replied, her voice still quivering.

"I have a request," he told her.

"Name it."

"The next time you want me to spank you, just say it. Don't pretend to leave some papers behind – talk to me about it."

Her entire body tensed, and she looked at him to tell him that he was wrong, but from the look on his face, she guessed that lying to him now would be a bad idea.

"Yes, sir, I will."

"Good." And as he comforted her, they shared their first kiss in what would turn out to be a long and happy relationship.